Triethylamine → HCID 178522111, compound

Participants

Reaction Steps

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (2.21 g, 5.82 mmol) was added to a stirred mixture of 3-(benzyloxy)cyclobutanecarboxylic acid (0.80 g, 3.88 mmol), 2-aminopyridine (0.73 g, 7.76 mmol), and triethylamine (1.08 mL, 7.76 mmol) in DMF (15 mL). The reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was separated, washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified via silica gel chromatography to give the separated diastereomers trans-3-(benzyloxy)-N-(pyridin-2-yl)cyclobutanecarboxamide and cis-3-(benzyloxy)-N-(pyridin-2-yl)cyclobutanecarboxamide.

Provenance & Evidence